My Brother's Best Friend
by NotaPunk
Summary: Gabriel Milton hasn't been back to his childhood home since he left for college, now after a one night stand, he learns how much he has missed out on. Rated M for future chapters, warnings this is Slash Fiction. Don't like, don't read.
1. Chapter 1

**NotaPunk: ****Hi everyone! Hope you all are having a lovely day, thank you so much for choosing '' for your fanfiction needs!**

**Disclaimer;**** I do wish that I owned Supernatual, but alas! I do not!**

**Pairings**

**Gabriel/Sam(Main)**

**Gabriel/Kali**

**Dean/Cas**

**Lucifer/Sam (One sided)**

**Tessa/Kali**

**John/Mary(Past)**

**Bobby/Ellen**

**Jo/Chuck**

**Michael/Meg(Married)**

**Raphael/Virgil**

**Anna/Balthazar**

**Main Characters**

**Gabriel Milton**

**Sam Winchester**

**Kali Sharma**

**Dean Winchester**

**Castiel Milton**

**Tessa McKeon**

**John Winchester**

**Mary Winchester**

**Bobby Singer**

**Ellen Singer**

**Jo Singer**

**Chuck Shurley**

**Anna Milton**

**Raphael Milton(Girl Raphael, cuz she is my secret addiction 0.0)**

**Michael Milton**

**Lucifer Milton**

**Meg Milton**

**College Visit**

Gabriel sat next to his best and possibly the greatest friend, Kali, under a tree, watching the passing High school seniors, on their campus tours. The Indian beauty had wanted to catch a look at the possible incoming fresh meat, to see if there was anyone fuck worthy. The duo leaned against the tree, both taking mental notes of individuals that piqued their interests.

Kali started humming a tuneless song when suddenly she elbowed Gabe in the side. He glared at her and she smiled teasingly at him, letting her eyes go back into the crowd, she lifted one elegant finger and pointed at a tall figure in the crowd. "Gigantor over there seems like your type," she smirked at her slightly taller friend.

Golden eyes rolled before the landed on 'Gigantor', and boy was he glad they did. Kali was right when she said that he was Gabe's type, all tall and athletically built. Stupid shaggy hair and dimples. He also had that geek boy virgin thing going for him, yum. Gabriel licked his thin lips unconsciously as he pulled out a sucker from his pocket.

He jumped up and winked at Kali, letting her enjoy the impending show. Kali rolled her eyes, not even bothering to try to hide her smirk, she had seen the kid earlier in the morning, and knew where to be so Gabe could work his 'magic'. Maybe she'd get some time today to try her luck with the cute junior that lived down the hall from her room.

Gabe slid himself into the unsuspecting crowd and made his way next to 'Gigantor'. The dirty-blonde haired man made work of sucking loudly on his sucker, catching everyone's attention, especially the Sasquatch next to him. The younger man looked at Gabriel, blinking several times before returning to look at the speaker.

Gabriel recognized the guy leading the tour as 'Some guy' who was in most of his classes, but never attracted much of Gabe's attention. He was painfully average, mouse brown hair, dull brown eyes, average height, average sense of humor, average grades, just so damn average! The only thing that was not average about him was his ability to make everything absolutely boring as soon as he opened his mouth.

The shorter male pulled out another sucker and made work on it. He looked out of the corner of his eye to see 'Gigantor' looking absolutely bored with the tour and even trying to hide a yawn. Gabe laughed to himself when the taller man failed. The brunette noticed that Gabe was laughing at him and turned a lovely shade of pink. Gabe patted his shoulder, sending him a sympathetic look before standing on his tip-toes to reach his ear, "It's okay to yawn, everyone else has."

The man shook his head, the leaned down to whisper in Gabriel's ear, "No, everyone is asleep. What you're hearing is snoring."

So, 'Gigantor' had a sense of humor. "Want a more exciting tour," asked Gabe, his eyebrows waggling.

'Gigantor' laughed quietly, "I'm guess you would be the guide?"

"Damn Skippy you lucky Sasquatch!" If 'Gigantor' had been insulted by the term Sasquatch, he didn't show it. In fact, he seemed to particularly enjoy it.

The man leaned down once more to Gabriel's ear, his breath ghosting over his skin, "Let's start with your room first, Squirt." The blonde shivered at his words, and gave the brunette a smirk before pulling on his hand to follow him. They snuck past the group with ease.

Kali rolled her eyes at her friend's luck. The guy just had to suck on some candy, tell a really bad joke, and flirt, and he was half way into a person's pants. It was truly unfair; she had been after the same girl since the beginning of sophomore year, with no signs of the girl even knowing she existed. If Kali was to be honest with herself though, she would've realized that actually knowing said girl's name would've increased her chances.

Gabriel awoke an hour later to the sound of rustling clothes; he turned his head and watched as his partner was getting dressed. "Where are you going? Am I _that _bad of company?"

The younger man jumped and quickly to turned to face the bleary eyed male. He smiled, revealing his dimples, "It isn't you, trust me" he ran his eyes appreciatively up and down Gabe's body, "it isn't you at all. If I stay here any longer I'm going to miss my bus back home."

Gabe smirked satisfied and extremely blissed out. He rolled out of bed and slid on his boxers, "Good to know, and please know that you are welcome to my bedroom anytime." He sauntered over to the taller man, leaning into his body, standing on his tip-toes and wrapping his arms around the man's neck, pulling him in for a peck on the lips.

'Gigantor' blushed and gave Gabe's mouth the same treatment. Their pecks started lasting longer and becoming open mouthed kisses. The younger man groaned before pushing away, "If you keep doing that, you're going to make me late."

The older man shrugged and smiled cheekily. He finally got the chance to look at 'Gigantor', and really look. The man looked familiar, like Gabe should know who he was, that he had piqued his interest in the past. The innocently round hazel eyes, the dimpled smile, the stupid shaggy hair, and the two freckles on his face. They all seemed too familiar. But Gabriel shrugged to himself, letting the younger man leave.

**NotaPunk; ****Sam is 18 in this, so no worries! Most of the other characters and maybe some plot will be introduced in Chapter 2! BTW I'm having trouble deciding on Gabriel's and Kali's majors, so if anyone has any suggestions that'd be great! ^^**


	2. Chapter 2

**NotaPunk; ****Hi everyone! The decision for majors won't be announced this chapter, sorry -_-' I just have a lot of research to do with it.**

**Disclaimor: You seriously have problems if you think I own Supernatural. Like fo real real, not play play!**

**The Ride Home**

When Gabriel saw his little brother Castiel again, there was a large chance that Castiel would be punched. Hard and in the face. And Gabriel would laugh. That was a day that he would look forward to, and would celebrate for years afterward.

Or atleast his butt would. The fourth born Milton child would not call being stuck inside a train for hours fun. Nor would he call going home for summer break fun either, or even a break. Gabriel had left Sioux Falls as soon as he could, he hated that place. More specifically he hated his family being stuck in a small area for too long.

All of Gabriel's childhood memories that were associated with his home town, all came with flashbacks of his family fighting. They were a very volatile bunch. The only person that he can remember who never was in a fight, verbally or physically, with another Milton, was his uncle Joshua.

Now, just because Gabriel said that he hadn't been to his home town, that doesn't mean that he hasn't seen his family. He has, every single year for Thanksgiving, Easter and summer break. They just were never in Sioux Falls. For those occasions that his family did see eachother, they would go to a resort in or out of the country. And everyone would usually go off to do their own thing.

That had worked PERFECTLY for everyone, until Castiel's turn to pick had rolled around. This year, he decided to be a bag of dicks and stay home for summer break. Gabriel would have loved to gone to Norway this year, but no.

The blonde didn't even know why his brother wanted to stay home, sure he was quiet and on the shy side, and really just moped around on their vacation anyway. Seriously, no matter where they went, his lil' bro would hide somewhere and read or whatever he did. Gabriel never did ask.

Worst of all was that the blonde was stuck alone on a freaking train. When Gabriel was a child, he had alone of energy, time, and imagination. This carried on to when he grew older, which was bad for everyone around him. Which is why no one would pick him up on their way, and Gabriel had to ride in a train. By himself. Which is very boring.

The college student was tempted to call Kali and screw with her (maybe get some phone sex), but decided against it. Gabriel was going to his hell, and Kali was going to hers. His beautiful friend was forced to accompany her Grandmother on her trip to India, to visit some of her family.

Now, some people would just shrug this off, and say, 'Hey, she gets to see her family, travel, and hang with a sweet old lady, how hard is that?' Those people would be considered idiots. Kali was forced to go because no one else in her immediate family would travel with her Grandmother. The brunette wasn't even doing this out of the goodness of her heart; it was because her parents were black mailing her. Escort her Grandmother, or they would stop paying for half of her tuition that they promised.

Some would feel pity for Grandma Sharma, being disliked by her children and grandchildren for no fathomable reason. Those people would be idiots too. Grandmother Sharma was at one point a very kind and loving person. Her children's friends would come to her when Kali's parents weren't available, just to hang out. She used to be the life of the party, she was loved by everyone who met her and people would describe her as a generous person.

Over the years, something had changed within Grandmother Sharma, she became bitter and hateful. Nothing was ever good enough for her. She would even pit her children against eachother, and make up rumors so that they would fight. She didn't stop there. Grandma Sharma loved to play favorites with her Grandchildren as much as she liked to ridicule them. Kali was her favorite granddaughter to verbally abuse.

She would mock everything about her, from the way she dressed to the way she sat. She would tell her that she was ugly, dull and stupid. Kali could never do anything right if you asked her Grandmother.

As Gabriel thought about his friend's predicament, the more he felt upset. Why couldn't he and Kali just hang out this summer instead of being forced to see people who they barely talk to or even think about? The deeper Gabriel thought, the more and more he drifted off to sleep.

* * *

><p>Two brothers sat next to eachother in suffocating silence before the shorter of the two switched the radio on. The younger of the two rolled his dark eyes and switched it off, sending a glare towards his brother. "Would you please not do that?"<p>

The blonde rolled his eyes, "Glad to see the stick is still firmly in place."

"I see you're getting started already Lucifer."

"Look, I never asked you to pick me up, I asked for Raph or Gabe. Hell, I would have gladly taken Castiel or even Rachel over you! I even emphasized that I didn't want you to come! And you want to know why? Because you act like a dick, and that I should be falling all over myself to praise you! So, sorry I wanted to avoid talking in the first place by listening to some music."

There was no longer silence in the car, as the two oldest Miltons screamed at eachother the rest of the ride there.

**NotaPunk:**** Hope you enjoyed the second chapter; really this was just to introduce some characters and shove some information in. Fun fact, some of this story will be based on real events. Such as Michael's and Lucifer's fights, Kali's Grandmother, Gabriel's pranks, just to name a few examples.**


	3. Chapter 3

**NotaPunk: ****Chapter three and right before midnight! :D All updates will now be every Friday after eight. This will happen until after October 21****st****, and for a very important reason (besides me being lazy) my older sister is getting married! And me, along with her two other bride's maids, are going to help her so that she won't be stressed out. And my sister's wedding trumps updates. And speaking of sisters, this chapter is introducing the only female Milton child! Our favorite redhead, Anna!**

**Little Sister**

Balthazar stared at his girlfriend as she started unpacking her bag in his apartment. She pulled out a seemingly endless supply of clothes, hygiene products, books and other miscellaneous items. The blonde raised his eyebrow and raised his wrist watch to eye level. It was too early for this shit, especially before he made his coffee a little Irish.

He walked away from the beautiful red head and entered his kitchen. He scouted the cabinets and pantry to find them unsatisfyingly empty. He pinched the bridge of his nose and cursed under his breath. Of course she would hide his liquor before he woke up; she always hated having alcohol in the house. Something to do with it being too much of a temptation.

He shuffled back into the room where the red head was sorting through her things. He stretched again and rested his palm on his stomach and began rubbing it slowly. He stared at her as she continued her work, enjoying his view of her ass.

"Not that I hate you being here darling, but what the hell are you doing?"He finally asked as she slowed down in her work.

She turned around to face him, her dark eyes wide, realizing that he was up and she had not finished her work. Some of her hair fell into her face and her cheeks flushed a pretty pink. She opened and closed her mouth several times before deciding on what to say. She pushed her dark red hair behind her ear.

She looked down guiltily and her eyebrows furrowed, "I don't want to stay in the same house with all five of my brothers at the same time."

Balthazar raised his eyebrow his girlfriend's unusual behavior, "And you brought everything you own?"

"They are staying for the whole summer," she looked down and seemed to sink into herself, clearly ashamed that she was trying to avoid her family.

"And you couldn't stay somewhere else," Balthazar teased, knowing the right buttons to push.

Her head snapped up and she smirked playfully at him, "I thought that my boyfriend would have wanted me to stay with him!"

"Well go to his apartment then! I have a few sluts coming over later for a sexy party, and I don't need some girl with self-esteem to ruin the mood," the blonde crossed his arms and winked.

Anna threw her head back and laughed, walking over to him. She wrapped her arms around his waist and he wrapped his arms around her shoulders. She rested her chin on his chest and stared at him, her smile wide and her eyes shining, "So I can stay?"

Balthazar kissed her on her forehead, "Okay, just don't let my girlfriend know. She the jealous type, you know?"

**NotaPunk: ****Just a small update to introduce Anna and Balthazar in the story.**


	4. Chapter 4

**NotaPunk:**** This chapter is slightly longer, thank Chuck! And Gabe is back in the chapter! Just one chapter without writing about him made me feel dirty and unclean *shivers*, it was freaky man! **

**Big Sister  
><strong>

Gabriel smirked as he walked beside his older sister, Raphael. She was taller than he was, only by an inch, but teasing eachother about their height difference was a habit of theirs. And having her hold up a sign that read, "Mr. Shrimp" had made him feel right at home. They skipped the usual hug and opted instead to stage an obviously fake kung-fu fight. After they scared the people at the station, the two siblings went on their way.

As the passed through the throngs of people, Gabriel couldn't help but notice the attention his sister was getting. It wasn't unusual, she was extremely beautiful after all, but the way they looked at her was unnerving. They looked like they were surprised to even see her just walking around. Gabriel opened his mouth to ask the dark skinned beauty what all that was about, when he was pushed into a bush.

He groaned and glared up at a stern faced older man. "What the hell Virgil," yelled Raphael.

His deep voice rumbled as he answered, though his expression remained the same, his eyes held a fear in them. Like a child that was about to be scolded by their teacher. "Orders were to-"

"I don't give a shit what orders were, that's my brother you dolt," Raphael interrupted him, her glare was fierce and fear filled both men's hearts.

Gabriel groaned as he sat up, yeah he was an asshole, but he didn't want his big sister to defend him. He was an adult now and had been fighting his own battles for awhile. He rolled his golden eyes, "Hey now Wonder Woman, it was a mistake no big deal." _Besides I'll get him back later, _he mentally added.

Virgil relaxed and rushed over to the shorter man up, when Gabe looked at the older man a thought struck him. Virgil reminded him of his father. The patriarch of the Milton family was a silent, stern man, who seemed complete emotionless and unsympathetic to outsiders. His family knew different, anything he wanted to say, anything that he couldn't say aloud, you could just look into his eyes, and understand. On the outside, Virgil's features were schooled into a calm expression. His eyes told another story, they held embarrassment and apologies.

* * *

><p>Gabriel sat next to his sister in the back of her car, Virgil was in the front, driving. He kept silent, and his eyes would look at the siblings through his rearview mirror every so often. The dark haired blonde smirked to himself; the older man's eyes would always wander towards his sister. Gabe recognized the look; he had seen it when his father looked at his mother, and when Anna talked about her Brit.<p>

Raphael frowned when she noticed that her brother wasn't paying attention to her, she pursed her lips and tugged on his collar, pulling him toward to her. Her yelped in surprise and sent a glare to her. Raphael smirked and opened her mouth to let loose a string of teasing when her eyes fell upon several marks on his neck. The dark pools that were her eyes widened and her mouth fell into an 'o'.

Gabriel noticed what his sister saw and pulled back to fix his color, a smirk forming on his thin lips. "What's wrong Sis, you act like you never saw a hickey before," teased Gabe, "We both know that isn't true." Gabe added with a wink, his gold eyes sparkled.

Raphael rolled her eyes, "True, but dear little brother, aren't you still a virgin? I can't imagine anyone would want to 'tap dat ass'. Don't tell me that you were playing with the vacuum again."

He scoffed, "I'll have you know that I am a very sexy guy! Kali has said so herself-"

The dark haired beauty cut him off, "She's your bro, and she doesn't count."

Gabriel continued without missing a beat, "And I can assure you dear sister, I don't even own a vacuum."

Raphael rolled her eyes, "Obviously. Now who marked your pretty neck?"

"Just this sexy Sasquatch. That's all you're getting, so you better change the subject." Gabriel said, getting bored with the subject. He would rather brag all about his one-night stand when the whole family was around, it would be so deliciously awkward.

Raphael pouted playfully, "You're no fun! Fine, who do you think will throw the first punch this time? My money is on Zach."

"That guy has no spine, no; I think it's going to be Luci again," answered Gabe, not even taking a moment to blink.

His sister just huffed, "Boring! Mike and Luci are in desperate need of couple's therapy."

"They both just need to be separated. They aren't that bad if they are doing their own thing. I guess they can't really do that this time, all of us being stuck in the same house and all. Why are we doing this vacation again," asked Gabriel.

"Because it's Castiel's turn, and mother spoils him." They both knew the last part wasn't true, but it was too much fun to tease the youngest Milton about being a Momma's boy.

Gabriel snorted and shook his head, "Kid seriously needs a hobby. Why did he want to stay home anyway? Nothing interesting there."

"You remember Sam, right?"

An image went before Gabriel's eyes of a thirteen year old boy, with puppy dog hazel eyes. He was too short for his age, and only had his brother's oversized hand-me-downs to wear. He had dark shaggy hair that he would allow to fall over his eyes when he was upset. The kid was Castiel's only friend, and would get adorably upset when teased.

"Sammy Winchester? Do they have a thing or something?" Gabriel smiled to himself, picturing the two younger boys holding hands or attempting to kiss.

Raphael got the same look, but it turned sour quickly, "Who knows, anyway, the past year was their last year in highschool, and next year they are going to different colleges. So I guess Cas wanted to spend summer with him."

Gabriel just 'hmmmed' to himself, and allowed his mind to wander back to childhood memories. More specifically of cute hazel eyed boys and their dimples.

**NotaPunk: ****Yep, yep, yep. I got nothing to say. :P**


	5. Chapter 5

**NotaPunk; ****It's another chapter! YAY! Sorry if there are any misspellings, I accidentally cut both of my thumbs to I'm typing with my other fingers. It's kind of hard, I now know how my dog feels when she tries to play video games, except she's adorable! :D**

**Little Sammy Winchester**

Lucifer was relieved when he and his brother finally made it to their childhood home. He jumped out of the car as fast as he could; slamming the door once he was out. Michael glared at him and Lucifer was tempted to flip him off, but decided to just smile innocently. Michael huffed and turned around, muttering something about ungrateful brats, completely missing the dirty look that Lucifer threw him.

The younger of the two brothers glared as the older walked into the house, ignoring the fact that Lucifer still had his luggage in the trunk of his car. The dirty blonde was tempted to go right up to his brother and punch him in his smug face, until that is he saw another car pull up. It was black and sleek, and a model that Lucifer couldn't give a name to. He only knew basic car models, and even his knowledge on those was limited.

When the car pulled up next to Michael's, Lucifer could see a grim faced man driving it. After the car was parked and turned off, the man came out and walked to the back, opening the doors. Raphael and Gabriel stepped out, both thanking the man. Lucifer walked over to his siblings, a smirk playing on his lips, Gabe was his favorite brother just as Raph was his favorite sister.

He looked directly at his younger sister, "Hello there Dr. Milton, I see you have a new cabaña boy." The elder Milton nodded his head in Virgil's direction as he opened up the trunk to retrieve Gabriel's luggage.

Raphael smirked sourly, she was used to her older brother's teasing, she took brunt of her older brother's 'love' when she was a self conscious teenager. "And I see you are still-"

Before she could finish her insult, Gabe elbowed her in the side, sending her a look. Raph huffed and rolled her eyes as she stomped her way through the front door. Virgil ran after her quickly, like the faithful friend he was.

"Couldn't you wait until after we all settle in," Gabriel asked his brother, already tired of talking with him. Lucifer was a bag of dicks after all.

Lucifer smirked at his younger brother and shrugged his shoulders lazily, "What fun would that be?"

Gabriel smirked right back at his brother, "Not much, but I would love it if we didn't have an apocalyptic family dinner for once."

The Milton brothers laughed with each other as they walked into the house. An older woman with graying strawberry blonde hair ran into the front hall. She wore a pair of capris, and a salmon colored button down blouse. A frilly apron was tied around her waist, and oven mitts were on her hands.

Her dark brown eyes widened with happy surprise when she saw two of her sons, she tore of her mittens and ran over to them. She pulled them into a tight hug, which both men readily reciprocated. She pulled back, one hand on the older blonde's shoulder and the other on Gabe's cheek. Her palms were still warm from baking.

She puckered her thin lips and kissed both of them on their cheeks. "OH! I've missed you both so much! I saw Raph come in with Virgil; she said you two were getting your luggage! Oh come in! Come in!" She ushered the two men into the kitchen, where Raphael sat in one of the chairs, one leg crossed over the other lazily. Next to her sat Virgil, he sat stiff as a board, gripping a little too tightly onto his mug of coffee.

Across from them sat Michael and his wife Meg. Meg had a mug of her own, though she had a flask in her pocket filled with her favorite whiskey, just in case her husband decided to get into a verbal fight with one of his family members.

Gabriel never understood how the two had gotten together; both had personalities that one would think that would clash constantly. Everyone liked Meg, with the exception being Zachariah, who didn't like anybody. Meg was a free spirit, after high school she hitch hiked across the whole North Americas (this was when she cut her hair off and dyed it blonde) earning an awesome tan, she rebelled against her parent and their expectations of what a woman should be. Before she settled down in Chicago, where she worked nights as a bartender and her days as a tattoo artist.

Michael was compulsive, he needed to do things a certain way, he followed orders to a T and the most rebellious thing he had ever done was get a half sleeve done when he was going to college in Chicago. He was a police officer on his way on becoming detective, he was religious, and cared too much for his father's approval.

The two had been married for only three years, after Michael wore Meg down. They had dated on and off after that, long distance. Michael wouldn't have been able to live with himself if they had had premarital sex, fearing disapproval from his parents. In fact, the first time that the two spent the night with eachother was the vacation when Meg was introduced to the family. After they were married, Michael moved to Chicago.

Meg was five foot five without heels, and had pale skin. She had long dark hair that curled slightly, and dark brown eyes that were almost black. All of the Miltons knew from various vacations, that she had several tattoos to go along with her beautiful figure.

Michael was five foot eleven, and had a lean muscular body and a smooth tan from his love of working outdoors and working out. He had dark hair like Grandpa Milton, but blue eyes like several of the other younger Miltons. His half sleeve was made up of different Celtic symbols. So visually, they made a very appealing couple.

Gabriel could tell that his sister-in-law was ready to just drink out of the flask herself because of the conversation topic. Raphael's job. Raphael's choice in careers had been a controversial issue in the family on a number of reasons. She was a doctor, yes, but she also worked in an abortion clinic once a month. This sparked much debate and burned many bridges in the Milton family.

Michael was about to go back to 'conversation' when Castiel came into the kitchen. He was still in his pajamas which consisted of blue boxers and a white tee-shirt. His short dark hair was a mess, and he had light stubble on his face. He yawned, stretching his arms in the air. He waved hello to everyone and grabbed a bowl from the cupboard.

Momma Milton pecked him on the cheek and handed him the milk along with the cereal. He rubbed one blue eye as he poured his overly sugary breakfast into the bowl, then the milk. Most of his older siblings stared as he ate. Cas had never gotten much sleep, but the dark circles under his eyes seemed darker that day, actually making him look pale.

Momma Milton smiled lovingly at him, "I hope you and Sammy didn't stay up too late last night, you haven't gotten any sleep for a while mister."

"It's Sam mom. You know he doesn't like being called Sammy. We didn't, just talked about different college visits and stuff. Then got everything ready for today we're-"

Lucifer and Gabriel laughed hard, interrupting him; Lucifer was the first to recover, "Sam? As in little Sammy Winchester? He's here?"

"And he kept you up all night? Nice one little brother!" Cheered the shortest male of the Milton family, "Is he still here?"

Castiel frowned and glared at his brothers, as the others rolled their eyes and smiled playfully, "He's taking a shower-"

Gabriel smiled even wider, imagining the different pranks that he pulled on the younger Winchester when he was in the shower, "I have to see this!"

Lucifer nodded, remembering all the times of teasing the dimpled brunette, "Just for old times' sake!"

Castiel looked as he was about to protest but both men took up running to the stairs. They snuck to the bathroom door, listening until the water finally turned off. Gabriel grabbed onto the door knob and they both busted through the door. "Hey little Sam-"

Gabriel stopped mid-sentence, his eyes widening as they ran over a familiar body and face. The broad shoulders, muscles everywhere, long legs, and stupid hair. The dark blonde felt his mouth drop open, the memories of their night together ran through his mind. Heat ran across his cheeks as he stared, realization hit him, and he suddenly felt nausea mixed with arousal.

**NotaPunk: ****Naked Sam! And awkward situations! Who doesn't love that? No yelling about Raphael's job! I made her a doctor because; in angel lore Raphael was the Angel in medicine. Seemed like a good fit. And there are going to be issues with the different careers that everyone has, because of different opinions. **


	6. Chapter 6

**NotaPunk: School is almost over, I don't know whether to be excited or not. I actually enjoy school again, even though it takes time from other things that are important to me. But it also inspires me and helps me become a better author. Anyway, this scene is a bit more graphic then the others so far. Sorry if it isn't very good.**

**Get Out!**

Water droplets ran down lean muscles, making the teen shiver from the cool air that hit his exposed skin. His nipples began to harden, as goose bumps formed on his chilled skin. His dark brown hair was heavy with water and stuck to his face as more water fell.

They ran down his strong neck, going past his Adam's apple, and over his pectorals. They graced his nipples, making the buds harden even more so, they slid past his well sculpted abs and down to his powerful legs. They followed the curve of every muscle, mesmerizing the two men that came through the door, just seconds before hand. One of his large hands was in his hair, pushing his bangs out of his face to reveal confused hazel eyes.

His mouth was agape, slightly, forming a soft 'O'. His cheeks were darkened with embarrassment, though it was hard for one to tell, his skin was a beautiful shade of olive-. The man hood he sported was long and thick as it hung heavily between his thighs. He looked so innocently delicious and so ripe for the taking.

Gabriel would have assumed the man was a virgin by his attitude, but he had firsthand experience that stated otherwise. He remembered strong hands, and taking turns being on top. They had gone through a bottle of lube that Gabriel had recently purchased.

Lucifer didn't know this of course, and the idea of breaking the Adonis that stood before him made him hard. More so then he would like to admit to himself. The blonde stared as air entered and left the nude male's body, getting harder at the idea of making said male pant his name.

Hazel eyes widened a fraction more, before narrowing, "Get. Out. Now", he bit out the order as he glared at the older men. The surprise had worn out, leaving only annoyance and embarrassment in its wake.

Gabriel gulped; the idea of teasing Sam died and was buried quickly. He grabbed his older brother by the back of the collar and pulled him out. He shoved the taller man down the stairs.

Lucifer caught his footing as he stumbled. He turned to glare at his now pale faced younger brother. He looked like he was going to puke any second now. Lucifer took the hint and shrugged as he continued his trek down the stairs. The blonde mentally added finding out what was going on with Gabe on his list of things to do. Right after seeing Sam Winchester naked again, of course.

The short man ran back to the bathroom and entered without even daring to ask permission. Sam had a towel wrapped around his waist and he was drying his shaggy hair out with another towel. Gabriel looked at him through the mirror, the idea of looking him in the eye suddenly revolting, "When were you going to tell me who you were?"

Sam sent the shorter man a confused look through the mirror as well, but did not stop his task. "I didn't know it was you. It's been years since we last saw eachother Gabe. And I planned on what we did being a onetime thing."

Gabriel nodded his head dumbly; he had had a similar train of thought. Though that didn't mean that he would mind a repeat performance. Sammy was quite good for a-. All thought processes stopped then sped up again, a new wave of nausea hitting the older man.

Gabriel stared wide eyed at the younger man in the mirror, fear and self hatred radiating off of him. "You were a virgin."

Sam turned to the short man, his eyebrows furrowed and his nose wrinkled in confusion, "What?"

"I-I stole your innocence," Cried Gabriel.

Sam turned to face him all the way, the task of drying himself forgotten for the time being, "Excuse me?"

The silly man dropped to his knees and clasped his hands in prayer, "Please forgive me! Our Father who art in heaven, hallowed be thy name-"

Sam rolled his eyes and turned back to the mirror, "I wasn't a virgin."

Relief flooded Gabriel, but so did confusion soon after, "Thank God! Wait-what?"

"You're the third person I've been with, and the second guy," Sam said nonchalantly as he examined his appearance.

"Who's the fir- Oh no! It was Castiel, wasn't it? First I steal his best friend who now turns out to be his boyfriend, then I come here acting like I'm so freaking awesome, ready to rub my latest-," disappear befell Gabriel. He was an ass to his siblings but he would never go this low to humiliate them.

"I've never dated Cas," interrupted Sam yet again.

Rage replaced guilt inside Gabriel, "You bastard! You stole my baby brother's innocence, and you don't have the balls to date him!"

"He's still a virgin."

* * *

><p>Kali felt as is her head was going to explode. After hours of being stuck with her over bearing harpy of a Grandmother, she was about to relax. She was so tired that she even decided to put off showering until the morning. She shucked her form fitting denim jeans off and slid out of her cotton top.<p>

Leaving herself in only her cloth sports bra and underwear, she stretched her arms above her head. A satisfying pop rang throughout the room and a smile came to her face.

She lazily slipped under the covers of her bed and letting her body relax even further. She nuzzled her head into her pillow and sighed contently. Her dark eyes slid closed, and she was falling deeper and deeper into slumber when she was interrupted. Gabriel's obnoxious ringtone, that he had created especially to annoy his best friend, echoed in the room.

Frustrated Kali pulled the phone from it charger and held it up to her ear, "There is a thirteen hour difference, so you better damn well tell me this is an emergency. A real one, not the 'I'm locked out of my car' shit."

A feminine voice answered, and sounded quite nervous, "Oh, um, I'm sorry. It's just; I was leaving the train station today and a found this phone. You were the most recent person in the history, and I wanted to give the owner back their phone."

Kali's face became warm and she felt as if she was going to explode from embarrassment, "I am so sorry! I thought it was my idiot friend calling me! I really can't help you, I'm in India right now, but I can call him at the place he's crashing at and tell him about you. Is that alright? Then you two can meet up and stuff."

The female voice spoke again, making Kali's heart skip a beat, "Okay, thank you."

The brunette gulped nervously, and calmed herself down before asking, "May I ask your name, so he doesn't think some creeper has his phone?"

"Tessa, Tessa McKeon."

**NotaPunk: So, I just wanted everyone to be forewarned that on the weekend of the 18****th**** there won't be an update, I'm going to be camping and one week in June there won't be an update because I'm going to be on vacation. Thank you for reading so far, please leave a review if you have the time. I'd like to know how I can do better, thank you.**


	7. Chapter 7

**NotaPunk; ****Hello everyone! I hope your week has been well! Next week I have several finals, my birthday, and a camping trip. There will be no update then or the week after because I have to work all week. I'm posting this early because this Friday I'm busy. This chapter will be kind of short, sorry, but I have to study. Things will be back to normal soon, thank you for your patience.**

**Meg's Annoyance**

Meg's fingers itched for the silver flask hidden in her purse. The day had been a stressful one, like all days where she had to send long amounts of time with her in-laws. It's not that they were bad people, just over zealous and opinionated. They all believed what they wanted to and never backed down, or even heard an argument from the opposing side.

Though she had a soft spot for a few of her relatives, like Cas, Gabe, her mother-in-law and many of the distant cousins that were still children. That had not been the case at dinner that night. Gabe had been acting like a total spaz and kept staring at Cas's friend the whole night. He looked like he was either going to throw up at any moment or jump the poor kid's bones. Cas in return set a steely warning glare to his older brother, and even went to sleepover at Sam's house. The only two argument buffers/ only people that could at least find safe topics incapacitated.

So, the poor mother of the bunch of lunatics actually tried to be a moderator. Meg wasn't sure who was crazier, the people arguing over such things instead of enjoying their time together, her mother-in-law for seeming to encourage it or Meg for ever agreeing to marry Michael.

Michael was such a kind, loyal man. There was such innocence and warmth from him that Meg never experienced within her life. Her parents were stuck in a loveless marriage because of their extreme religious beliefs that they went on ignoring each other. They never cheated on each other, or raised a hand. They had no passion for even the smallest of smiles.

They slept in separate bedrooms, went to work at different times, never ate together, and from her knowledge kissed each other. Whenever they looked into the other's eyes, there was this hollow look. The only passion that they seemed to have that related to the other was when one of their children was involved. Especially Meg. They had their ideals that were exactly the same, and that they wanted their children to immolate.

Meg knew that they had to have sex at one point. If they had sex, that didn't mean they had to be in love. And she knew that the man and woman who raised her were in fact her biological parents, as well as the biological parents to her sisters and brother. They each looked too much like each other for it to be otherwise. They all had their mother's dark brown, almost black eyes, along with her rose bud lips. They also had their father's smirk, and ears. Those were the most obvious features of course.

So, she had immolated her parent's relationship with her first two boyfriends, before changing that. She went on to toxic relationships then to being single with a few one night stands when she needed to let loose. She had all of her family's disapproval, and hadn't talked to any of them for the longest time. In fact, the only one that attended her wedding was her older sister Casey. Even then, she was subjected to questions like "Are you pregnant?" "Does he need a citizenship?" and her favorite, "This isn't like you, wouldn't you feel better back at your tattoo parlor?"

Michael was Meg's foil. He was her yin to her yang. Light to dark. Angel to demon. He was the peanut butter to her jelly. They just worked well together. Sure Meg was against marrying him at first, fear had seeped into her very soul at the thought of their relationship becoming like her parent's. It took a long time for either one to trust the other, to love each other, and when they did, Meg was afraid of it slipping through her fingers. Then one night, Michael had been shot and was in the hospital in critical condition. She wasn't allowed to see him until he was stabilized and went to recover in a normal room.

It was a nightmare for her and she knew that if it was to ever happen again, she would never forgive herself if she couldn't hold his hand one last time. The next spring they were married in Michael's hometown with his family, their friends and co workers to bear witness. For the longest time the couple lived in harmony until Michael, who always wanted to be a father, noticed how well Meg loved and got along with children. Michael in Meg's opinion would fit the 'Father Knows Best' role just fine; she just had a feeling of dread curl into her stomach when she thought about being a mother.

And of course the subject came up whenever they saw children, walked past a baby store or the park. Though, the subject would be dropped quickly most of the time, there were certain occasions that her husband would push it. Like when they would see his family, especially his younger cousins.

Meg laid on top of the queen sized bed and its brightly colored quilt. She was reading a book that she had gotten into, a psychological thriller, and had one of the many Milton children curled into her side, sound asleep. As the curly haired blonde snored lightly, Michael walked in on the scene. His eyes were still their usual soft blue shade, but warmed with such a life and happiness, Meg felt her heart skip a beat.

Michael always looked at her like that, like she was some sort of queen. But this look was different; this was his 'I want to be the father of your children' look. Meg had seen it so many times before, and each time it made her heart do the same thing. She opened her mouth to let loose a flood of sarcastic remarks to try to rid him of that look. He pressed his pointer finger gently to her lips, and tilted his head to the sleeping form next to her. The tattooed woman nodded her head and watched in fascination as he picked the child up gently in both of his arms, and carried him to his parents.

When he returned, she was stripping out of her jeans, deciding to just sleep in her form fitting tee-shirt. She wriggled her hips smoothly, and pushed her thumbs into the waist band, giving them soft tugs until they were at her knees. She was about to kick them off when she felt a familiar pair of hands on her hips and the face of her husband buried into the crook of her neck. Within minutes Meg was on her back, stark naked and Michael was in between her legs, still wearing his jeans.

She knew she should be angry, try to push her husband off, or at least demand he put on a condom. Any thought was lost though as soon as he had his hands on her. She was usually the aggressive one, the one that started it, the one who topped. This was different though, Michael was different. And Meg swore to herself, that she would be pissed later.

**NotaPunk: ****I love the pairings between angels and demons, mostly crack pairings though. Love those! So, of course I would pair the most badass of the female demons with one of the most goodie two shoes of the angels! Though you guys might like a future pairing hopefully.**


	8. Chapter 8

**NotaPunk:**** Why yes, I did make the last chapter all about Meg. Because I loooooove her! But, I love Castiel and there deserves to be a chapter with him as a main character, because, you know he is one! And thanks everyone for being patient, you are all amazing! I'm back in the saddle everyone!**

**Waking Up to Someone**

Castiel stared at the white ceiling of his bedroom. It was the only part of his room that was completely bare. The rest was filled with a mix between his and Sam's things, just as Sam's room was. Year after year, ever since Castiel had met the younger Winchester, the two had become so close. Castiel knew that he freaked people out and didn't have the social skills that many of his family members possessed, and the thought of being separated from his only friend scared him.

Sam laughed at Castiel's jokes, gave him his nickname, got him into baseball, went to all of his games and when Castiel went into the theater, showed up for every performance, even if he was bystander #2. Sam got him in a way that not even his family could or ever would. Sometimes he would think about the teasing, that he was in love with the taller teen, but he would shake his head. Sam was his best friend, his protector, and his confidante. Though Sam was everything Castiel would ever want or in a partner, the idea disturbed the blue eyed teen.

Even of the thought of the two of them kissing made his stomach queasy and sent chills down his spine. His affection and love for Sam ended at friendship, and brotherhood. He thought back to a science class that he had during freshman year; they were talking about what attracts someone to another person. The teacher had of course given them numerous theories, but one stuck with Castiel the most. People were attracted to those who mirrored attributes of those who meant the most to them.

Castiel turned on his side and looked at Sam, who was lying on a cot next to his bed. They used to share a bed together during their sleepovers, but when puberty hit, it suddenly became awkward. Especially because of the occasional morning wood.

Castiel thought back to his family. He was not a momma's boy or a daddy's boy. He loved each of his siblings equally but none stuck out in his mind. He didn't know his grandparents well enough, and he didn't spend a lot of time with his extended family. The most important person to him was Sam.

Whenever he would have to go away, he would write letters to everyone. But if there were only a few envelopes or stamps left, he would only write to Sam. During holidays he always strived to find the perfect gift for Sam, and he went out of his way to make Sam proud or smile. And he knew for a fact that the youngest Winchester did the same for him.

Castiel was pulled out of his thoughts when he heard a sound near his bedroom door, a scuffling of sorts. He sat straight up, allowing the blanket to slide off of his frame. He slowly got out of bed, reluctant to leave, but his curiosity got the better of him. The bottoms of his feet made contact with the cold, hard floor as he walked to the wooden door. He cracked the door open slightly, and glanced down to the noise.

There stood an anxious looking Jack Russell terrier. Castiel groaned and rubbed his tired face with the palm of his hand. The dog officially belonged to the whole family, and unofficially belonged solely to Gabriel. This didn't stop him from waking Castiel up every single morning to take him for his morning walk, even though there were many other options for the animal. Of course the dog had a name, Castiel just refused to call it by the monstrosity of a name that his siblings agreed on.

* * *

><p>Raphael smiled to herself as she watched her youngest brother leave the house with Lord Fergus the KitKat Kungfu Master Milton. She wasn't must of a dog person, but she loved that little fur ball to bits. He especially came in handy when she had to find out some information. She carefully made her way down the hallway, her silky night dress stopping just above her knees. It was a peach color, and had lace for the straps, hem and neck line.<p>

She stopped at Castiel's door, and gently twisted the knob, slipping in without a sound. She quickly caught sight of her target, and stood over him. She moved one long leg over his body, and moved down slowly. Both of her hands were on either side of his face, and stopped her from falling onto the sleeping teen.

With a sigh of relief she moved, letting herself rest her lower body against his sleeping form. He didn't seem to notice which gave her more courage, she lent down so that her lips were next to his right ear. "Sam, wake up." Her voice was as smooth as silk, and got the job done.

Sam awoke, and didn't jump until he saw who she was, and how close her face was. Red stained the younger man's cheeks, and his hazel eyes were wide. He made to get up, which Raphael stopped by rubbing herself against him. It did the trick, his body became rigid, and she could feel his groin harden. She clicked her tongue, "Shhhh, look Sam. I have some questions, and you are the only one that can give me some straight answers."

* * *

><p>Jo Singer woke up with the scent of her boyfriend engulfing her. She hummed lightly to herself and snuggled deeper into his side. He in turn tightened his hold on her, and brought her closer to him. Jo moved her head to get a better look at him. She giggled softly when during her movements his beard scratched her scalp lightly.<p>

She really did have a thing for men with beards and blue eyes, especially when they were as cute as Chuck Surely. Chuck used to be just someone she would see when she went to the local book store or library; he was a clerk in former and an almost constant fixture in the later. She really hadn't gotten to know him until last winter.

She had broken up with her most recent of asshole boyfriends, and was walking back to her house. It was freezing out, and when she left her now ex, she had also left her coat in an effort to get away from him, his grabby hands and car as soon as possible. She walked past many people, none of them noticing the drying tear tracks on her cheeks, her shivers or how alone she felt.

Jo was going to go sneak into her room and try to go unnoticed, but someone had different plans for her that evening. She had bumped into Chuck, and knocked many of his papers and books out of his arms. As she helped him gather her belongings, he noticed her appearance and took her to get some hot chocolate, not before slipping his coat onto her shoulders. He listened to her rant, and when it was time for her to go home he drove her back, he was so flustered that he forgot to take his coat back. Which led to their second meeting.

Jo stroked Chuck's hairy cheek as he slept on, not wanting to disturb him from his rest. His eye lids fluttered opened and he sleepily smiled at her, "Good morning."

Jo's smile grew and she pecked him on the lips, "Morning."

Chuck returned the smile full force before stretching his arms above his head, "What time is it?"

"Almost eight." Jo answered nonchalantly.

The scruffy man yelped and jumped out of bed, and went to the pile of discarded clothes that was at the end of Jo's bed. The blonde stared at her boyfriend as he panicked to get his clothes on, jumping and falling in attempt to pull his jeans on. She stood up and walked over to him calmly, "Sweetie, what's wrong?"

His eyes were wide with fear; he gulped once, his Adam's apple bobbing as he spoke, "Your parents are supposed to home today at eight!"

* * *

><p>Jo's brown eyes widened and she ran to help her boyfriend get dressed, and have all of his things ready. She had forgotten that today was the day of their return from their second honey moon. She was swamped with the end of the school year, and having the house to herself.<p>

Bobby glanced over at his wife; she was using his shoulder as a pillow as she slept. The older man smiled to himself, knowing how much Ellen deserved a break after driving most of the way home, even taking his first turn for driving. As he turned a corner he caught sight of Castiel walking his family's dog. He slowed down to a park and rolled down his window, surprised to see the boy since his family would usually be off on vacation in some ritzy spot.

"Hey Cas, what are you doing here," greeted Bobby, never one to bother to beat around the bush.

Castiel looked up, still in his boxers and T-shirt, "Hello Mr. Singer, I'm just walking the dog. How was the second honey moon?"

Bobby rolled his eyes, quickly getting annoyed with the youngest Milton's obliviousness and ignoring the question, "I can see that boy, but I want to know why you are still here in town?"

Castiel nodded his head, finally getting what the older man wanted, "Oh, it was my turn to pick the vacation spot, and I wanted to stay home for the summer so Sam and I could hang out before school started."

Ellen just awoke, and had half listened to the conversation, when she finally was able to ask, "Where is Sam?"

"Inside, I think he's still asleep," answered Castiel, shrugging his shoulders nonchalantly.

Bobby furrowed his eyebrows in a deep scowl, "You left him alone in a house full of Miltons?"

Castiel furrowed his own eyebrows and stared at Bobby, his head tilting. It was the same look that he always gave when he was confused by something, or extremely interested by something. He stood there for only three seconds before his blue eyes widened in realization and sprinted back to his house, the small dog by his side.

Ellen playfully rolled her dark eyes and snuggled into her husband's shoulder, "Cute kid. Strange, but cute." Bobby nodded in agreement as he started driving his truck again, looking forward to seeing his own strange but cute kid at home. He had a great time with his wife, the reconnected and had fun at the Bed and Breakfast. A place that Bobby thought would never be his cup of tea, he was proven wrong of course when the couple never left the room except for meals. But to be home again would be a relief. Or, that's what he was thinking until he saw Chuck Shurley drive out of his driveway.

**NotaPunk: ****I feel no regret about making Raphael this way, I tried to mix personality traits from Angelology and how the character is in Supernatural. A great sense of humor, she's sexy and she knows it, smart, protective of her family and will do anything to protect/embarrass the people she cares about. For those who want to know, Jo is seventeen and Chuck is twenty three. Since Sioux Falls is located in South Dakota, I would like to point out that the legal age of consent is sixteen. Besides, the most they have done is just sleep over at eachother's places and kiss.**


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